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【结 构 式】

【分子编号】35139

【品名】(3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl phenyl sulfone; [(3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl](dioxo)phenyl-lambda(6)-sulfane

【CA登记号】

【 分 子 式 】C23H32O5S

【 分 子 量 】420.57008

【元素组成】C 65.69% H 7.67% O 19.02% S 7.62%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Treatment of hydroxylactone (I) with benzyl bromide and silver oxide gave the corresponding benzyl ether (II). Subsequent reduction of the lactone (II) with LiAlH4 afforded the linear diol (III). Tioether (IV) was prepared by treatment of (III) with diphenyl disulfide and tributylphosphine, and the remaining hydroxyl group of (IV) was then protected as the ketal (VI) using ethyl vinyl ether (V) and pyridinium tosylate. Oxidation of (VI) to sulfone (VII) was accomplished with m-chloroperbenzoic acid. Condensation of (VII) with 2-methyl-delta-valerolactone (VIII), followed by BF3 - Et2O-catalyzed cyclization furnished spiroketal (IX). Finally, the phenylsulfonyl group of (IX) was reductively removed by means of sodium amalgam.

1 Oikawa, H.; et al.; Highly regio- and stereoselective reductions of spiroketals. Tetrahedron Lett 1993, 34, 33, 5303.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(I) 35134 (4S,5S)-5-(hydroxymethyl)-4-methyldihydro-2(3H)-furanone C6H10O3 详情 详情
(II) 35135 (4S,5S)-5-[(benzyloxy)methyl]-4-methyldihydro-2(3H)-furanone C13H16O3 详情 详情
(III) 35136 (3S,4S)-5-(benzyloxy)-3-methyl-1,4-pentanediol C13H20O3 详情 详情
(IV) 35137 (2S,3S)-1-(benzyloxy)-3-methyl-5-(phenylsulfanyl)-2-pentanol C19H24O2S 详情 详情
(V) 18762 1-Ethoxyethylene; Ethyl vinyl ether;Ethoxyethene 109-92-2 C4H8O 详情 详情
(VI) 35138 benzyl (2S,3S)-2-(1-ethoxyethoxy)-3-methyl-5-(phenylsulfanyl)pentyl ether; 1-([[(2S,3S)-2-(1-ethoxyethoxy)-3-methyl-5-(phenylsulfanyl)pentyl]oxy]methyl)benzene C23H32O3S 详情 详情
(VII) 35139 (3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl phenyl sulfone; [(3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl](dioxo)phenyl-lambda(6)-sulfane C23H32O5S 详情 详情
(VIII) 35140 3-methyltetrahydro-2H-pyran-2-one C6H10O2 详情 详情
(IX) 35141 (2S,3S,5R,6S,11R)-2-[(benzyloxy)methyl]-3,11-dimethyl-1,7-dioxaspiro[5.5]undec-5-yl phenyl sulfone; (2S,3S,5R,6S,11R)-2-[(benzyloxy)methyl]-3,11-dimethyl-5-(phenylsulfonyl)-1,7-dioxaspiro[5.5]undecane C25H32O5S 详情 详情
Extended Information